5-Chloro-1,2,3,4-tetrahydroisoquinoline → HCID 136237306, compound

HRID 713524Notes

Reaction equation

HRID 713524 reaction equation
[O:1]=[C:2]([NH:13][CH2:14][C:15]1[NH:16][C:17](=[O:25])[C:18]2[CH2:24][O:23][CH2:22][CH2:21][C:19]=2[N:20]=1)[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=O)[CH2:6][CH2:5]1.[Cl:26][C:27]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:28]=1[CH2:29][CH2:30][NH:31][CH2:32]2>>[Cl:26][C:27]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:28]=1[CH2:29][CH2:30][N:31]([C:10]([CH:7]1[CH2:8][CH2:9][N:4]([CH2:3][C:2]([NH:13][CH2:14][C:15]3[NH:16][C:17](=[O:25])[C:18]4[CH2:24][O:23][CH2:22][CH2:21][C:19]=4[N:20]=3)=[O:1])[CH2:5][CH2:6]1)=[O:12])[CH2:32]2

Participants

3

Reactant 2

HCID 125950835-Chloro-1,2,3,4-tetrahydroisoquinolineHCID 136627188HCID 136627188, compound

Product 1

HCID 136237306HCID 136237306, compoundYield 18%

Procedure

The title compound (44 mg, 18% yield) was prepared following the general procedure of Example 1 from 1-(2-oxo-2-((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methylamino)ethyl)piperidine-4-carboxylic acid (250 mg, 0.50 mmol) and 5-chloro-1,2,3,4-tetrahydroisoquinoline (84 mg, 0.50 mmol). 1H NMR (400 MHz, DMSO-d6) δ 8.20 (br. s., 1H), 7.32 (d, J=6.6 Hz, 1H), 7.22 (d, J=8.1 Hz, 2H), 4.74 (br. s., 1H), 4.64 (s, 1H), 4.34 (s, 2H), 4.18 (d, J=5.6 Hz, 2H), 3.66-3.87 (m, 4H), 3.09-3.20 (m, 1H), 2.95 (s, 4H), 2.79-2.91 (m, 2H), 2.73 (br. s., 1H), 2.67 (br. s., 1H), 2.02-2.23 (m, 2H), 1.74 (br. s., 4H). HRMS calculated for C25H30ClN5O4 500.2065. found (ESI, [M+H]+), 500.2066. Retention time=1.36 min.

Sources & evidence

ORD record
ord-64a1d9a8eed247e5b874be0224b197fa
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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